CN107434758A - Method for synthesizing monobromo condensed ring aromatic hydrocarbon compound - Google Patents
Method for synthesizing monobromo condensed ring aromatic hydrocarbon compound Download PDFInfo
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- CN107434758A CN107434758A CN201710367448.0A CN201710367448A CN107434758A CN 107434758 A CN107434758 A CN 107434758A CN 201710367448 A CN201710367448 A CN 201710367448A CN 107434758 A CN107434758 A CN 107434758A
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- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- 239000011259 mixed solution Substances 0.000 claims abstract description 12
- 229910001513 alkali metal bromide Inorganic materials 0.000 claims abstract description 10
- 239000000758 substrate Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 72
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001246 bromo group Chemical group Br* 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 16
- 238000004440 column chromatography Methods 0.000 claims description 14
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 12
- 239000003480 eluent Substances 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- 235000010265 sodium sulphite Nutrition 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical group [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 6
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- JAAGVIUFBAHDMA-UHFFFAOYSA-M rubidium bromide Chemical compound [Br-].[Rb+] JAAGVIUFBAHDMA-UHFFFAOYSA-M 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000001186 cumulative effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 238000007086 side reaction Methods 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 10
- 239000003814 drug Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
A method for synthesizing monobromo condensed ring aromatic hydrocarbon compounds comprises the following steps: taking a condensed ring aromatic hydrocarbon compound shown as a formula I as a substrate, adding alkali metal bromide, slowly adding ZnAl-BrO into a mixed solution of water and an organic solvent3 ‑LDHs, reacting for 5-7 h at 45-55 ℃, and after the reaction is finished, carrying out post-treatment on the obtained reaction mixture to obtain a monobromo fused ring aromatic hydrocarbon compound shown in a formula II; the condensed ring aromatic hydrocarbon compound shown in the formula I, the alkali metal bromide and the ZnAl-BrO3 ‑The mass ratio of the substances of LDHs is 1: 0.6-0.8: 0.7-1.2, and the brominating reagent is a solid substance, is cheap and easy to obtain and is environment-friendly; the reaction condition is mild; the post-treatment is convenient, and the reaction operation is simple; the atom utilization rate and the selectivity are high; high yield of target product and less side reaction.
Description
Technical field
The present invention relates to a kind of synthetic method of organic compound, and in particular to synthesizes single bromo condensed-nuclei aromatics class to one kind
The method of compound.
Background technology
Condensed-nuclei aromatics halide is as a kind of important raw material or intermediate in essences such as medicine, agricultural chemicals, dyestuff and spices
It is widely used in thin product chemistry.In all kinds of condensed-nuclei aromatics halide, bromine compounds because its reactivity is of a relatively high, and
Bromine atoms are as a kind of leaving group easily sloughed, with the organic compound of bromine substitution for a long time in organic synthesis
Since be considered as one kind have important value synthon either presoma, either in laboratory still in the industrial production
Usage amount is larger, including the coupling of the keys such as C-C, C-N, C-O.In addition, they are either had radioactivity as medicine
Diagnostic flag in drug therapy using extensive, closed so the method for preparing brominated organic compound is always chemist
The content of note.
In existing document report, majority using bromine or NBS as bromine source come synthetic bromide for condensed-nuclei aromatics class chemical combination
Thing.But using bromine it is intrinsic the shortcomings that be reaction in there is half bromo element to generate corrosive bromine product HBr, the theory of bromine
Utilization rate only has 50%, the serious wasting of resources be present, and the reaction often needs to add the Louis such as metal break flour or bromide
This acid is used as catalyst, further pollutes the Green Chemistry for not meeting existing promotion；Although NBS is kind of a safer bromo
Reagent, but its preparation process is complicated, and preparation cost is higher, and generally makes in use along with special chemical auxiliary agent
With so can not spread among actual production process.
Although prior art discloses the various methods for preparing single bromo condensed-nuclei aromatics class compound, these methods are universal
There are one or more shortcomings such as：Severe reaction conditions, yield is relatively low, and the reaction time is longer, and selectivity of product is low, operation
And post processing intricate operation etc..
The content of the invention
To overcome the shortcomings of the single bromo condensed-nuclei aromatics class compound of existing synthesis and shortcoming, it is an object of the invention to provide
A kind of new method for synthesizing single bromo condensed-nuclei aromatics class compound.
The present invention uses following scheme：
A kind of method for synthesizing single bromo condensed-nuclei aromatics class compound, methods described are carried out as follows：With shown in formula I
Condensed-nuclei aromatics class compound be substrate, add alkali metal bromide, in the mixed solution of water and organic solvent, then slowly plus
Enter ZnAl-BrO3 -- LDHs, 5~7h is reacted at 45~55 DEG C, TCL tracking reaction process, after reaction terminates, gained reaction is mixed
The post-treated process of compound obtains single bromo condensed-nuclei aromatics class compound shown in formula II；Condensed-nuclei aromatics shown in described formula I
Class compound, alkali metal bromide and ZnAl-BrO3 -The ratio between-LDHs amount of material is 1:0.6~0.8:0.7~1.2,
Further, described alkali metal bromide is lithium bromide, sodium bromide, KBr, rubidium bromide or cesium bromide, is preferably
KBr.
Further, the organic solvent is that the one or more in dichloromethane, toluene, ethyl acetate, acetonitrile, acetic acid are appointed
The mixed solution of meaning ratio.
Further, the volumetric usage of the mixed solution of described water and organic solvent is with the condensed-nuclei aromatics class thing shown in formula I
The amount of matter is calculated as 7.5~10ml/mmol.
Further, the volume ratio of described water and organic solvent is 1：13~19.
Further, the mixed solution of preferably described water and organic solvent is that volume ratio is 1:5:9 water, dichloromethane
And the mixed solution of acetic acid.
Further, the reaction temperature of the condensed-nuclei aromatics class compound shown in preferably described formula I is 50 DEG C, and the reaction time is
6h。
Further, condensed-nuclei aromatics class compound, alkali metal bromide and the ZnAl-BrO shown in preferably described formula I3 --
The ratio between LDHs amount of material is 1:0.6:0.9.
More specifically, after reaction terminates, after described reactant mixture is using sodium sulfite solution washing, dichloromethane
Extraction, merge organic phase, crude product is obtained after being concentrated under reduced pressure, gained crude product is with petroleum ether：Ethyl acetate=10~15:1 conduct
Eluant, eluent, through column chromatography for separation, obtain single bromo condensed-nuclei aromatics class compound shown in target product formula II.
Compared with prior art disclosure, the beneficial effects of the present invention are：
Bromide reagent of the present invention is solid matter, cheap and easy to get, and environmentally friendly；Reaction condition is gentle；After locate
Reason is convenient, and operation is simple；Atom utilization is high, and selectivity is high；Target product yield is high, and side reaction is few.
Embodiment
In order that creation feature, technological means, purpose and effect of the present invention are easy to understand, with reference to embodiment
The present invention is described further and explains, but specific embodiment is not limitation of the present invention.
Embodiment 1
By pyrene (404mg, 2mmol), KBr (143mg, 1.2mmol), acetic acid 9ml, water 1ml, dichloromethane 5ml it is mixed
Close solution sequentially add with condenser pipe, thermometer three-neck flask in, be transferred in heated at constant temperature magnetic agitation water-bath,
ZnAl-BrO is slowly added in 15min in batches3 -- LDHs (1.8g, 1.8mmol), controlling reaction temperature are 50 DEG C, TCL tracking
Reaction process, after reaction terminates, washed using sodium sulfite solution, then extracted, be associated with using dichloromethane (3 × 10ml)
Machine phase, two medicine spoon column chromatography silica gels (200-300 mesh) are added in dichloromethane phase, are evaporated under reduced pressure away organic solvent, logical
Cross column chromatography (petroleum ether：Ethyl acetate=15:1 is used as eluant, eluent) isolated target product 383mg.White solid, yield
68%.
Characterize data：Fusing point：148-150.1H NMR(500MHz,CDCl3)δ:8.46 (d, J=9Hz, 1H), 8.25 (t, J
=8Hz, 3H), 8.20 (d, J=9Hz, 1H), 8.12 (d, J=9Hz, 1H), 8.08-8.02 (m, 3H)
Embodiment 2
By pyrene (404mg, 2mmol), lithium bromide (104mg, 1.2mmol), acetic acid 9ml, water 1ml, dichloromethane 5ml
Mixed solution sequentially add with condenser pipe, thermometer three-neck flask in, be transferred in heated at constant temperature magnetic agitation water-bath,
Slowly add ZnAl-BrO in batches in 15min3 -- LDHs (1.8g, 1.8mmol), controlling reaction temperature be 50 DEG C, TCL with
Track reaction process, after reaction terminates, washed using sodium sulfite solution, then extracted using dichloromethane (3 × 10ml), merged
Organic phase, two medicine spoon column chromatography silica gels (200-300 mesh) are added in dichloromethane phase, are evaporated under reduced pressure away organic solvent,
Pass through column chromatography (petroleum ether：Ethyl acetate=15:1 is used as eluant, eluent) isolated target product 371mg.White solid, production
Rate 66%.
Characterize data：Fusing point：148-150.1H NMR(500MHz,CDCl3)δ:8.46 (d, J=9Hz, 1H), 8.25 (t, J
=8Hz, 3H), 8.20 (d, J=9Hz, 1H), 8.12 (d, J=9Hz, 1H), 8.08-8.02 (m, 3H)
Embodiment 3
By pyrene (404mg, 2mmol), sodium bromide (124mg, 1.2mmol), acetic acid 9ml, water 1ml, dichloromethane 5ml it is mixed
Close solution sequentially add with condenser pipe, thermometer three-neck flask in, be transferred in heated at constant temperature magnetic agitation water-bath,
ZnAl-BrO is slowly added in 15min in batches3 -- LDHs (1.8g, 1.8mmol), controlling reaction temperature are 50 DEG C, TCL tracking
Reaction process, after reaction terminates, washed using sodium sulfite solution, then extracted, be associated with using dichloromethane (3 × 10ml)
Machine phase, two medicine spoon column chromatography silica gels (200-300 mesh) are added in dichloromethane phase, are evaporated under reduced pressure away organic solvent, logical
Cross column chromatography (petroleum ether：Ethyl acetate=15:1 is used as eluant, eluent) isolated target product 377mg.White solid, yield
67%.
Characterize data：Fusing point：148-150.1H NMR(500MHz,CDCl3)δ:8.46 (d, J=9Hz, 1H), 8.25 (t, J
=8Hz, 3H), 8.20 (d, J=9Hz, 1H), 8.12 (d, J=9Hz, 1H), 8.08-8.02 (m, 3H)
Embodiment 4
By pyrene (404mg, 2mmol), KBr (143mg, 1.2mmol), acetic acid 9ml, water 1ml, dichloromethane 5ml it is mixed
Close solution sequentially add with condenser pipe, thermometer three-neck flask in, be transferred in heated at constant temperature magnetic agitation water-bath,
ZnAl-BrO is slowly added in 15min in batches3 -- LDHs (1.8g, 1.8mmol), controlling reaction temperature are 45 DEG C, TCL tracking
Reaction process, after reaction terminates, washed using sodium sulfite solution, then extracted, be associated with using dichloromethane (3 × 10ml)
Machine phase, two medicine spoon column chromatography silica gels (200-300 mesh) are added in dichloromethane phase, are evaporated under reduced pressure away organic solvent, logical
Cross column chromatography (petroleum ether：Ethyl acetate=15:1 is used as eluant, eluent) isolated target product 360mg.White solid, yield
64%.
Characterize data：Fusing point：148-150.1H NMR(500MHz,CDCl3)δ:8.46 (d, J=9Hz, 1H), 8.25 (t, J
=8Hz, 3H), 8.20 (d, J=9Hz, 1H), 8.12 (d, J=9Hz, 1H), 8.08-8.02 (m, 3H)
Embodiment 5
By pyrene (404mg, 2mmol), KBr (143mg, 1.2mmol), acetic acid 9ml, water 1ml, dichloromethane 5ml it is mixed
Close solution sequentially add with condenser pipe, thermometer three-neck flask in, be transferred in heated at constant temperature magnetic agitation water-bath,
ZnAl-BrO is slowly added in 15min in batches3 -- LDHs (1.8g, 1.8mmol), controlling reaction temperature are 55 DEG C, TCL tracking
Reaction process, after reaction terminates, washed using sodium sulfite solution, then extracted, be associated with using dichloromethane (3 × 10ml)
Machine phase, two medicine spoon column chromatography silica gels (200-300 mesh) are added in dichloromethane phase, are evaporated under reduced pressure away organic solvent, logical
Cross column chromatography (petroleum ether：Ethyl acetate=15:1 is used as eluant, eluent) isolated target product 371mg.White solid, yield
66%.
Characterize data：Fusing point：148-150.1H NMR(500MHz,CDCl3)δ:8.46 (d, J=9Hz, 1H), 8.25 (t, J
=8Hz, 3H), 8.20 (d, J=9Hz, 1H), 8.12 (d, J=9Hz, 1H), 8.08-8.02 (m, 3H)
Embodiment 6
By pyrene (404mg, 2mmol), KBr (143mg, 1.2mmol), acetic acid 6ml, water 1ml, dichloromethane 4ml and second
Acetoacetic ester 5ml mixed solution sequentially add with condenser pipe, thermometer three-neck flask in, be transferred to heated at constant temperature magnetic force and stir
Mix in water-bath, slowly add ZnAl-BrO in batches in 15min3 -- LDHs (1.8g, 1.8mmol), controlling reaction temperature
For 25 DEG C, TCL tracking reaction process, after reaction terminates, washed using sodium sulfite solution, then using dichloromethane (3 ×
10ml) extract, merge organic phase, two medicine spoon column chromatography silica gels (200-300 mesh) are added in dichloromethane phase, are evaporated under reduced pressure out
Organic solvent is removed, is passing through column chromatography (petroleum ether：Ethyl acetate=15:1 is used as eluant, eluent) isolated target product
377mg.White solid, yield 67%.
Characterize data：Fusing point：148-150.1H NMR(500MHz,CDCl3)δ:8.46 (d, J=9Hz, 1H), 8.25 (t, J
=8Hz, 3H), 8.20 (d, J=9Hz, 1H), 8.12 (d, J=9Hz, 1H), 8.08-8.02 (m, 3H).
Claims (9)
- A kind of 1. method for synthesizing single bromo condensed-nuclei aromatics class compound as shown in formula II, it is characterised in that described preparation Method is：Using the condensed-nuclei aromatics class compound shown in formula I as substrate, alkali metal bromide is added, in the mixed of water and organic solvent Close in solution, be slow added into ZnAl-BrO3 -- LDHs, 5~7h is reacted at 45~55 DEG C, after reaction terminates, gained reaction is mixed The post-treated process of compound obtains single bromo condensed-nuclei aromatics class compound shown in formula II；Condensed-nuclei aromatics shown in described formula I Class compound, alkali metal bromide and ZnAl-BrO3 -The ratio between-LDHs amount of material is 1:0.6~0.8:0.7~1.2,
- A kind of 2. method for synthesizing single bromo condensed-nuclei aromatics class compound as claimed in claim 1, it is characterised in that：Described Alkali metal bromide is lithium bromide, sodium bromide, KBr, rubidium bromide or cesium bromide.
- A kind of 3. method for synthesizing single bromo condensed-nuclei aromatics class compound as claimed in claim 1, it is characterised in that：It is described to have Solvent is the mixed solution of dichloromethane, toluene, ethyl acetate, acetonitrile, one or more arbitrary proportions in acetic acid.
- A kind of 4. method for synthesizing single bromo condensed-nuclei aromatics class compound as claimed in claim 1, it is characterised in that：Described The cumulative volume dosage of the mixed solution of water and organic solvent is calculated as 7.5~10ml/ with the amount of the condensed-nuclei aromatics class material shown in formula I mmol。
- A kind of 5. method for synthesizing single bromo condensed-nuclei aromatics class compound as claimed in claim 1, it is characterised in that：Described The volume ratio of water and organic solvent is 1：13~19.
- A kind of 6. method for synthesizing single bromo condensed-nuclei aromatics class compound as claimed in claim 3, it is characterised in that：Described The mixed solution of water and organic solvent is that volume ratio is 1:5:The mixed solution of 9 water, dichloromethane and acetic acid.
- A kind of 7. method of synthesis list bromo condensed-nuclei aromatics class compound as described in claim 1~6, it is characterised in that：Institute The reaction temperature of condensed-nuclei aromatics class compound shown in the formula I stated is 50 DEG C, reaction time 6h.
- A kind of 8. method of synthesis list bromo condensed-nuclei aromatics class compound as described in claim 1~6, it is characterised in that：Formula I Shown condensed-nuclei aromatics class compound, alkali metal bromide and ZnAl-BrO3 -The ratio between-LDHs amount of material is 1:0.6:0.9.
- A kind of 9. method for synthesizing single bromo condensed-nuclei aromatics class compound as claimed in claim 1, it is characterised in that：Reaction knot Shu Hou, after described reactant mixture is using sodium sulfite solution washing, dichloromethane extraction, merges organic phase, be concentrated under reduced pressure Crude product is obtained afterwards, and gained crude product is with petroleum ether：Ethyl acetate=10~15:1 is used as eluant, eluent, through column chromatography for separation, obtains Single bromo condensed-nuclei aromatics class compound shown in target product formula II.
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| CN108299149A (en) * | 2018-03-06 | 2018-07-20 | 棓诺(苏州)新材料有限公司 | The synthetic method of high-purity O LED intermediate 1- bromine pyrenes |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299149A (en) * | 2018-03-06 | 2018-07-20 | 棓诺(苏州)新材料有限公司 | The synthetic method of high-purity O LED intermediate 1- bromine pyrenes |
| CN108299149B (en) * | 2018-03-06 | 2021-03-02 | 棓诺(苏州)新材料有限公司 | Synthesis method of high-purity OLED intermediate 1-bromopyrene |
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